US3682914A - 2,6-diphenyl-4,5-dihydro-3(2h)-pyridizinone derivatives - Google Patents
2,6-diphenyl-4,5-dihydro-3(2h)-pyridizinone derivatives Download PDFInfo
- Publication number
- US3682914A US3682914A US777882A US3682914DA US3682914A US 3682914 A US3682914 A US 3682914A US 777882 A US777882 A US 777882A US 3682914D A US3682914D A US 3682914DA US 3682914 A US3682914 A US 3682914A
- Authority
- US
- United States
- Prior art keywords
- group
- derivative
- dihydro
- pyridazinone
- methoxyphenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- NUPJVFNTHQXDSZ-UHFFFAOYSA-N 2,6-diphenyl-4,5-dihydropyridazin-3-one Chemical class O=C1CCC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 NUPJVFNTHQXDSZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002429 hydrazines Chemical class 0.000 claims abstract description 5
- KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical class OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
- -1 2-(p-methoxyphenyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone Chemical compound 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- KPIOFCJOKUHZPF-UHFFFAOYSA-N (3-methoxyphenyl)hydrazine Chemical compound COC1=CC=CC(NN)=C1 KPIOFCJOKUHZPF-UHFFFAOYSA-N 0.000 claims description 2
- IHOVXDZBTLPBEX-UHFFFAOYSA-N 2,6-bis(4-methoxyphenyl)-4,5-dihydropyridazin-3-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)CCC(C=2C=CC(OC)=CC=2)=N1 IHOVXDZBTLPBEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 claims 1
- RMTYJLWDVSGYDC-UHFFFAOYSA-N (4-methylsulfanylphenyl)hydrazine Chemical compound CSC1=CC=C(NN)C=C1 RMTYJLWDVSGYDC-UHFFFAOYSA-N 0.000 claims 1
- ZODFRCZNTXLDDW-UHFFFAOYSA-N 4-(4-bromophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Br)C=C1 ZODFRCZNTXLDDW-UHFFFAOYSA-N 0.000 claims 1
- AHVASTJJVAYFPY-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C=C1 AHVASTJJVAYFPY-UHFFFAOYSA-N 0.000 claims 1
- OMTDIBZSUZNVJK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1 OMTDIBZSUZNVJK-UHFFFAOYSA-N 0.000 claims 1
- QMUOWXJYDYHHLJ-UHFFFAOYSA-N 6-(4-bromophenyl)-2-(4-methylphenyl)-4,5-dihydropyridazin-3-one Chemical compound C1=CC(C)=CC=C1N1C(=O)CCC(C=2C=CC(Br)=CC=2)=N1 QMUOWXJYDYHHLJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 18
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000002365 anti-tubercular Effects 0.000 abstract description 3
- 230000002155 anti-virotic effect Effects 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 229960000583 acetic acid Drugs 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229960004909 aminosalicylic acid Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ROUCRNBAMZECST-UHFFFAOYSA-N 1-methyl-1-thiophen-2-ylhydrazine Chemical compound CN(N)C1=CC=CS1 ROUCRNBAMZECST-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical group C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60B—VEHICLE WHEELS; CASTORS; AXLES FOR WHEELS OR CASTORS; INCREASING WHEEL ADHESION
- B60B23/00—Attaching rim to wheel body
Definitions
- R represents a member selected from the group of from 1-4 carbon atoms consisting of a lower alkyl group of from 1-4 carbon atoms, a lower alkoxy group of from l-4 carbon atoms and a lower alkylthio group of from l-4 carbon atoms;
- R represents a member selected from the group consisting of hydrogen and a methyl group;
- X represents a member selected from the group consisting of a halogen atom and a lower alkoxy group.
- the invention also comprises a process for the production of the above-described novel pyridazinone derivative which comprises reacting, under heating, a hydrazine derivative represented by the following formula:
- R is' as heretofore defined; or reacting a salt of the hydrazine derivative described thereof with a B-benzoylpropionie acid derivative represented by the following formula:
- reaction may be performed in a non solvent, or an organic solvent, generally in the presence of a condensing agent.
- the present invention comprises a novel 2,6-diphenwherein R represents a lower alkyl group of from l-4 carbon atoms a lower alkoxy group of from l-4 carbon atoms or a lower alkylthio group of from l-4 carbon atoms; R represents a hydrogen or a methyl group of from 1-4 carbon atoms and X represents a halogen atom and a lower alkoxy group.
- the present invention also comprises a process for the production of the aforesaid novel pyridazinone derivative in good yields by reacting, under heating, a hydrazine derivative represented by general formula NHNH2 R1 (It) wherein R is as above defined; or reacting a salt thereof with a fi-benzoylpropionic acid derivative represented by general formula (III) X R2 (III) wherein X and R are as above defined, in a non-solvent, or an organic solvent generally in the presence of a condensing agent.
- the present process proceeds even without a solvent, but it may preferably be carried out in a suitable solvent.
- solvents there are employed organic acids, such as acetic acid, formic acid, propionic acid, lactic acid, butyric acid and the like; hydrocarbon solvents such as cyclohexane, n-hexane, benzene, toluene and the like; general organic solvents such as dioxane, dimethylformamide and the like; and alcohols such as methanol, ethanol, propanol and the like.
- the reaction usually proceeds in the temperature range of from about 50 to about 200C, but 60l00 C. is most preferred.
- the reaction may even be carried out in the absence of a condensing agent but the use of the condensing agent is desirable to obtain good yields of the product.
- condensing agents used in the present invention there are illustrated mineral acids, such as hydrochloric acid, sulfuric acid, phosphoric acid, and the like; Lewis acids such as zinc chloride, copper chloride, borofluorides and the like; polyphosphoric acids; cation exchange resins; etc.
- the 2,6-diphenyl-4,5-dihydro-3(2H)-pyridazinone derivatives of this invention are novel compounds that have never been reported in the literature, and show remarkable anti-inflammatory, anti-tuberculous and antivirus activities, with minimum toxicity.
- the 2-( p-methoxyphenyl)-6-(pchlorophenyl)-4,5-dihydro-3(2H)-pyridazinone of this invention exhibits a potential inhibition of carrageenininduced edema in rats hind paws with lower acute toxicity per OS, in comparison with the most notable antiinflammatory drug, phenylbutazone (1,2-diphenyl-3 ,5- dioxo-4-n-butylpyrazolidine) as follows:
- PAS p-aminosalicylic acid
- R methyl group, ethyl group, isopropyl group, methoxy group, ethoxy group, methylthio group and ethylthio group.
- X chlorine atom, bromine atom and methoxy group.
- Typical examples of the 2,6-diphenyl-4,5-dihydro-3 (2H )-pyridazinone derivatives of the present invention are, for example, 2-(p-methoxyphenyl)-6-(pchlorophenyl)-4,5-dihydro-3(2H)-pyridazinone, 2-(ptolyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)- pyridazinone, Z-(p-methylthiophenyl)-6-(pchlorophenyl)-4,5-dihydro-3(2H)-pyridazinone, 2-(pmethoxyphenyl)-6-(p-bromophenyl)-4,5-dihydro- 3( 2H )-pyridazinone, 2-( p-tolyl )-6-(p-bromophenyl 4,5-dihydro-3(2H)-pyridazinone, Z-
- EXAMPLE 2 A mixture of 9 g. of p-methoxyphenylhydrazine, 12.7 g. of ,B-(p-methoxybenzoyl) propionic acid, 2 ml. of glacial acetic acid, and 45 ml. of benzene was heated under reflux for 15 minutes. Benzene was removed to yield a residue, which was heated at -107C., for 6.5 hours in 45 ml. of glacial acetic acid contained about 3. g. of hydrogen chloride. Recrystallization (twice) from ethanol gave 9.5 g.
- R may have from one to four carbon atoms, and all examples were performed under normal pressure.
- a 2,6-diphenyl-4,5-dihydro-3(2H)-pyridazinone derivative having the formula wherein R represents a member selected from the group consisting of a lower alkyl group of from 1-4 carbon atoms, a lower alkoxy group of from 14 carbon atoms, and a lower alk ylthiogroup of from l-4 carbon atoms; R is a member selected from the group consisting of hydrogen and a methyl group; and X represents a member selected from the group consisting of a halogen atom and a lower aloxy group.
- a process for the production of a 2,6-diphenyl- 4,5-dihydro3(2l-l)-pyridazinone derivative represented by the general formula wherein R, represents a member selected from the group consisting of a lower alkyl group of from 1-4 carbon atoms, a lower alkoxy group of from 1-4 carbon atoms, and a lower alkylthio group of from 1-4 carbon atoms; R is a member from the group consisting of hydrogen atom and a methyl atom; and X represents a NHNH:
- B-benzoylpropionic acid derivative is selected from the group consisting of B-(p-chlorobenzoyl)propionic acid, ,B-(pbromobenzoyl)propionic acid and B-(p-methoxybenzoyl)propionic acid.
- organic solvent is selected from the group consisting of acetic acid, formic acid, propionic acid, lactic acid, butyric acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7525967 | 1967-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3682914A true US3682914A (en) | 1972-08-08 |
Family
ID=13571028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US777882A Expired - Lifetime US3682914A (en) | 1967-11-22 | 1968-11-21 | 2,6-diphenyl-4,5-dihydro-3(2h)-pyridizinone derivatives |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3682914A (enrdf_load_stackoverflow) |
| DE (1) | DE1810200B2 (enrdf_load_stackoverflow) |
| FR (1) | FR1604863A (enrdf_load_stackoverflow) |
| GB (1) | GB1218640A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289774A (en) * | 1978-10-19 | 1981-09-15 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Lipid lowering and anti-thrombotic 6-arylpyridazin-3-ones and a process for their preparation |
| US6399611B1 (en) * | 1995-04-20 | 2002-06-04 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Arylalkylpyridazinones |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3317530A (en) * | 1963-02-06 | 1967-05-02 | Basf Ag | 4-nitro-5-hydroxypyridazones-(6) and a process for their production |
-
1968
- 1968-11-14 FR FR1604863D patent/FR1604863A/fr not_active Expired
- 1968-11-21 US US777882A patent/US3682914A/en not_active Expired - Lifetime
- 1968-11-21 GB GB55372/68A patent/GB1218640A/en not_active Expired
- 1968-11-21 DE DE1810200A patent/DE1810200B2/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3317530A (en) * | 1963-02-06 | 1967-05-02 | Basf Ag | 4-nitro-5-hydroxypyridazones-(6) and a process for their production |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289774A (en) * | 1978-10-19 | 1981-09-15 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Lipid lowering and anti-thrombotic 6-arylpyridazin-3-ones and a process for their preparation |
| US6399611B1 (en) * | 1995-04-20 | 2002-06-04 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Arylalkylpyridazinones |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1218640A (en) | 1971-01-06 |
| FR1604863A (enrdf_load_stackoverflow) | 1972-04-17 |
| DE1810200B2 (de) | 1974-08-01 |
| DE1810200A1 (de) | 1970-01-22 |
| DE1810200C3 (enrdf_load_stackoverflow) | 1975-04-03 |
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